The 'Contrarian Manager'

For the past couple of months I’ve been working on a project to build a new company/venture together with a venture builder. And i’ve tried using my very latest iteration in my ‘company building’ philosophy.

And so far the results are in my view awesome. Not just for the venture…but for what they say about the future of how I think many companies will operate.

We’ve taken this whole remote work thing… and taken it to its extreme.

Meanwhile I’ve taken much of the traditional ways of thinking about ‘management’ and i’ve basically trampled on them.

First some context on this venture

We started about two months ago and were live after the first week or so. Using a platform that is available as a SaaS.

Even though it is live… I prefer not to mention the company for now. It’s not that i’m going through much effort to hide it.. but it affords me some flexibility to not directly publicize it for now.

I’ll publicize it relatively soon.

Also we are about 15 people in total, all part-time, many of them Upwork. So what I call a ‘traditional Ken setup’ lol.

What are the rules I applied?

Rule 1: We don’t try to build relationships

• I met nobody in person and only met a few of the folks during a brief 5-10 minute call when I first hired them (on Upwork). Many of the folks I never even met them on a call.
• I also dont try to get to know them and make zero attempts at building any type of relationships in the team outside of our work interactions. Why? Because I view it as counterproductive (i’ll explain more later).

Rule 2: We don't do team meetings or 1-on-1's

• There are no team meetings. There are no regular 1-1’s. Ever.
• If I need to communicate with someone urgently I typically slack them. Once in a awhile if its a complex topic we’ll jump on a Slack Huddle (I think i’ve made a total of 4 such calls in ~2 months)

Rule 3: We make zero effort at culture

• No team parties. No sayings on our walls. Nothing.
• But there is still strong respect and teamwork. I don’t need to talk about being respectful to others because I demonstrate it. And drop the hammer very quickly when i see it not being upheld.

Rule 4: We execute tasks in a very systematic way

• Everything that takes more than 10 minutes to do is reflected in a task in Clickup (our project mgmt system). And is clearly written out with a context and goal.
• There is a tree-like structure to the folders where tasks are organized.
• Tasks have a clear assignee, a due date, and updates as comments.

If there is no task I consider the activity to not exist. If there is no commented update, I consider nothing to have been done. I keep it simple ;)

Rule 5: We are extremely responsive

• My rule is that everybody clears Clickup notifications at least 1-2x per day. This results in everyone responding in a timely way to one another.
• Also on Slack i encourage everyone to respond very quickly. Meaning if I don’t get a response from someone within a day i ping them again and ask why.
• I lead by example.. i’m very fast at responding on either Clickup or Slack and either giving clear direction or unblocking them.

Rule 6: Updates are constant but very little time is invested

• I don’t ask anyone to write me special updates. Because their updates are the comments they make on the Clickup cards.
• And I follow all the Clickup cards that i’m interested in.
• Meaning I literally go through hundreds of Clickup notifications every day.

Rule 7: Transparency, Transparency, Transparency

• The end results is that everything the team does is transparent to me.
• And the investor is directly tagged on all tasks that are relevant to them. So they spend probably 10-20 minutes a day just clearing and commenting on Clickup notifications.
• We hide nothing and rather look to engage the investor by being so transparent.

The Five Outcomes

Outcome 1: Its the most productive team i've perhaps ever been a part of

• We have gotten a lot done in two months. You’ll just need to take my word on it for now.
• There are no wasted reports or busy work. Nobody has ever even opened up PowerPoint.

Outcome 2: No politics

• When folks don’t know each other and don’t know me… you would be surprised at how little politics there are.
• It’s like we have killed the soil upon which politics grows. Because politics are rooted in human relationships. And we don’t really let relationships form (beyond responding to each others’ tasks).

Outcome 3: Almost no conflict

• I haven’t had to settle a dispute between members of the team once.
• Why? Because they just get their stuff done. And are not politicking because we are all just freelancers. And it will always stay that way.

Outcome 4: Strong loyalty and happiness of the team

• A lot of folks will be looking at this saying to themselves… “This is BS. I bet Ken has created a team of mercenaries who don’t care about the work they are doing.”
• But then if I showed you our Clickup or Slack… you’d see that you were outright wrong. They care a lot and work hard to do a good job.
• In part because I vetted them and let go of all the folks that didn’t care about what they do or had a bad attitude (which is very fast to do on Upwork).
• Also, I put together a team of folks who like being judged for what they ‘do’ and not what they ‘say’ or how well they build relationships.
• And has anyone wanted to leave or show any sign of discontent yet? No.

Outcome 5: Very low operating costs

• I’m using freelancers and only paying them for what they do (either by hour or by scope of work).
• It keeps operating costs very low.

What you can take away from this?

I’m not trying to convince anyone to work this way. In fact I hope you do not. Because i view it as my competitive advantage. My ‘moat’ if you will.

And I honestly would put my way of working up against any team out there that is doing something similar.

Does this work for every single industry and team? Probably not. But I think you’d be surprised just how often it WOULD work if it was implemented correctly.

Also, in the coming years I think more and more companies will realize the things I have.

That humans are complex relationship-based creatures… but this means that some people will like each other and others will not.

And its nearly impossible to scale a team where everyone likes each other. So politics will develop. And that will erode teams.

I’ve literally seen it in every company i’ve ever been employed at.

And i’m pretty sure I’ve stumbled across the closest thing to the cryptonite that prevents that whole vicious cycle from happening. And creates a team that just loves getting shit done.

I read a really good Business Insider article a couple weeks back that talks about how many GenZ-ers don’t like their managers and so they flip jobs much faster than any generation before it.

And because of this tons of highly talented people are having their careers ruined. They’re not good at getting along with their managers or with perhaps their team’s culture.

But does that make them bad at what they do? No. Maybe they are awesome, but just need the system that allows them to demonstrate it?

That is the future that I see and that I wanna contribute to.

Humans are getting more complex with each generation… not less. It’s high time we created a management system that accounts for that.